What Do You Want Your Money to Say After You're Gone?

Two extremes, one third path

I meet people at both ends. Some accumulate endlessly, driven by a fear that no number will ever be safe. Others spend as though the balance will refill itself. Both extremes are exhausting, and neither produces peace.

There is a third path I call the Radical Middle: enough to live well, enough to sleep soundly, and the freedom to give with purpose.

What the Radical Middle actually requires

It requires a number. Not a vague sense of comfort — an actual figure, tested against inflation, taxes, longevity, and the life you intend to live. Once that number exists, everything above it becomes available for purpose instead of anxiety.

Sharon, a supply-chain executive I worked with, spent decades in a 60-hour-a-week enforcement role. What changed for her wasn't a return; it was seeing on paper that she only had a few more years to go. Each planning meeting was, in her words, like pulling into a charging port. She retired in her fifties. The last time we met, she was headed to do yoga by the lake.

Legacy is a message, not a transfer

Ask what you want your money to say after you are gone. To your children. To your church or community. To the institutions you care about.

Then work backward:

• Which values do I want the structure to reinforce — work, generosity, education, stewardship?
• What should my heirs know about why, not just how much?
• What can I give now, while I can watch it work?

Tax efficiency matters. It is a tactic. The deeper question comes first, and answering it is what turns accumulation into meaning.